title: Stereoselective synthesis of amido and phenyl azabicyclic derivatives via a tandem aza Prins-Ritter/Friedel-Crafts type reaction of endocyclic N-acyliminium ions.
abstract: A simple protocol is described for the synthesis of amido and phenyl hexahydroindolizin-3(2H)-one, hexahydro-1H-quinolizin-4(6H)-one, and 1,3,4,10b-tetrahydropyrido[2,1-a]isoindol-6(2H)-one derivatives via endo-trig (aza-Prins type) cyclization followed by an intermolecular Ritter/Friedel-Crafts reaction of cyclic N-acyliminium ions, which are derived from the boron trifluoride etherate treatment of regioselectively reduced N-homoallyl imides. The reactions are highly diastereoselective with excellent yields.
authors.affiliation: Department of Chemistry Indian Institute of Technology Guwahati , Guwahati, Assam 781039, India.
authors.forename: Kiran
authors.initials: K
authors.lastname: Indukuri
authors.forename: R
authors.initials: R
authors.lastname: Unnava
authors.forename: Manash J
authors.initials: MJ
authors.lastname: Deka
authors.forename: Anil K
authors.initials: AK
authors.lastname: Saikia
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007212:Indolizines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D053961:Azabicyclo Compounds; D007212:Indolizines